Smoking product having flavorant additive



United States Patent ()fiice 3,334,637 Patented Aug. 8, 1967 3,334,637 SMOKING PRODUCT HAVING FLAVORANT ADDITIVE Donald L. Roberts, Winston-Salem, N.C., assiguor to R. J. Reynolds Tobacco Company, Winston-Salem, N.C., a corporation of New Jersey No Drawing. Filed Dec. 8, 1964, Ser. No. 416,923 14 Claims. (Cl. 13117) This invention relates to tobacco and has for an object the provision of a tobacco composition having improved aroma and flavor.

It is well known in the tobacco art that the domestic tobaccos which are exemplified by burley, Maryland, fluecured, bright leaf or Virginia tobaccos are low in flavor as compared with so-called oriental or aromatic tobaccos which are imported from Turkey, Greece, Bulgaria, Yugoslavia, Rhodesia and Russia. Accordingly, it has been common practice in the tobacco industry to prepare blends of domestic and oriental tobaccos in order to provide cigarettes which have desired flavor and aroma characteristics. Accordingly, it is a further object of this invention to provide a domestic tobacco which has an enhanced flavor and aroma.

An additional object of this invention is to provide a tobacco which has been treated in such manner as to impart a subtle flavor which is pleasing to the smoker.

In accordance with one embodiment of this invention a domestic tobacco is provided to which has been added a small amount of l-methyl-Z-pyrrolecarboxaldehyde. The above chemical, herein referred to as Compound I, may be represented by the followingformula:

The chemical Compound I indicated above can be synthesized by the alkylation of pyrrolecarboxaldehyde. A detailed description of the synthesis of Compound I is as follows:

The procedure of Treibs and Dietl, Ann., 619, 80-95 (1958) was used in which 2-pyrrolecarboxaldehyde (52.4 grams) was converted to the sodium salt using metallic sodium in toluene. The sodium salt (50 grams) was then placed in 1000 milliliters of ether and 50 milliliters of dimethyl sulfate in 200 milliliters of ether was added dropwise. After refluxing two hours, the solution was filtered and the filtrate was stirred for eight hours with 50 percent aqueous potassium carbonate. The mixture was then separated and the dried ether layer was distilled. Vacuum distillation gave 15.2 grams [boiling point 76 per 11 millimeters of mercury; lit., boiling point 72.4 per 12 millimeters of mercury] or 25 percent yield of Compound I.

Compound I is a liquid having a boiling point of approximately 72.4 C. per 12 millimeters of mercury pressure and the following characteristics:

Infrared spectrum: 3100, 2940, 1660, 1310, 1212, 1086,

1053, 1021, 763, and 742 cmf Nuclear magnetic resonance spectrum: 7=0.44(l), 3.14

(2, multiplet), 3.80 (1, triplet), and 6.05(3).

Mass spectrum: parent peak at 109.

In accordance with this invention, the designated Compound I is usually added to a domestic tobacco in amounts to provide a tobacco in which is dispersed about 0.001 to about 1.0 percent by weight of the additive. Preferably the amount of additive is between about 0.005 and about 0.03 percent by weight in order to form a domestic tobacco having a desired flavor and aroma. The preferred percentages may be somewhat less, however, if

other flavorants imparting a desired aroma are also employed. The additive may be applied in any suitable manner and preferably in the form of a liquid solution or suspension by spraying, dipping or otherwise. The additive may be incorporated at any step in the treatment of the tobacco, but is preferably added after aging, curing and shredding and before the tobacco is formed into cigarettes. Likewise, it will be apparent that only a portion of the domestic tobacco need be treated and the thus treated tobacco may be blended with other tobaccos before the cigarettes are formed. In such cases, the tobacco treated may have the additive in excess of the amounts above indicated so that when blended with other tobaccos the final product will have the percentage within the indicated range.

In accordance with one specific example of this invention, an aged, cured and shredded burley tobacco is sprayed with a one percent ethyl alcohol solution of the above indicated compound in an amount to provide a to bacco composition containing 0.01 percent by'weight of the additive on a dry basis. Thereafter the alcohol is removed by evaporation and the tobacco is manufactured into cigarettes by the usual techniques. The cigarette when treated as indicated has a desired and pleasing aroma which is detectable in the main and side smoke streams when the cigarette is smoked; this aroma is described by some smokers as an almond note.

It will be particularly apparent that the manner in which the additive is applied to the tobacco is not particularly important since, as indicated, it may be done in the form of spraying or dipping, utilizing suitable suspensions or solutions of the additive. Thus, water or volatile organic solvents, such as alcohol, ether, acetone, volatile hydrocarbons and the like, may be used as the carrying medium for the additive while it is being applied to the tobacco. Also, other flavor and aroma producing additives, such as those disclosed in Jones United States Patent No. 2,766,145 and Schumacher United States Patent No. 2,978,365, may be incorporated into the tobacco with the additive of this invention.

While this invention is particularly useful in the manufacture of cigarette tobacco, it is also suitable for use in connection with the manufacture of pipe tobacco, cigars and other tobacco products formed from sheet tobacco dust or fines which are well known to the art. Likewise, the additives of the invention can be incorporated with materials such as filter tip materials, seam paste, packaging materials and the like which are used along with tobacco to form a product adapted for smoking. Furthermore, the additive of this invention can be added to certain tobacco substitutes of natural or synthetic origin and by the term tobacco as used throughout this specification is meant any composition intended for human consumption by smoking or otherwise, Whether composed of tobacco plant parts or substitute materials or both.

Those modifications and equivalents which fall within the spirit of the invention and the scope of the appended claims are to be considered part of the invention.

I claim:

1. A domestic tobacco having added thereto a small amount of 1-methyl-2-pyrrolecarboxaldehyde suflicient to alter the flavor of the tobacco.

2. A domestic smoking tobacco having added thereto between about 0.001 and about 1.0 percent by Weight of 1-methy1-2-pyrrolecarboxaldehyde.

3. A domestic smoking tobacco having added thereto between about 0.005 and about 0.03 percent by weight of 1-methyl-2-pyrrolecarboxaldehyde.

4. A tobacco product having added thereto a small amount of 1-methyl-2-pyrrolecarboxalde'hyde sufiicient to improve the flavor of the tobacco.

5. A tobacco product having added thereto between 3 about 0.001 and about 1.0 percent by weight of l-methyl- 2-pyrrolecarboxaldehyde.

6. A tobacco product having added thereto between about 0.005 and about 0.03 percent by weight of l-methyl-2-pyrrolecarboxaldehyde.

7. A tobacco substitute having added thereto between about 0.001 and about 1.0 percent by weight of l-methyl- 2-pyrrolecarboxaldehyde.

8. A process of improving tobacco which comprises adding thereto a small amount of 1-methyl-2-pyrrolecarboxaldehyde suflicient to improve the flavor of the tobacco.

9. A process of improving the flavor of tobacco which comprises adding thereto between about 0.001 and about 1.0 percent of 1-methyl-2-pyrrolecarboxaldehyde.

10. The process recited in claim 9 wherein the stated percent is between about 0.005 and 0.03 percent.

11. A process of improving tobacco which comprises adding thereto in the form of a liquid solution a small amount of 1-methyl-2-pyrrolecarboxaldehyde sufficient to improve the flavor of the tobacco.

12. The process recited in claim 11 in which the small amount of the additive is between about 0.001 and 1.0. percent by weight.

13. A process of improving tobacco which comprises adding thereto in the form'of a liquid suspension a small amount of 1-methyl-2-pyrrolecarboxaldehyde suflicient to improve the flavor of the tobacco.

14. The process recited in claim 13 in which the small amount of the additive is between about 0.001 and 1.0 percent by weight.

References Cited UNITED STATES PATENTS 7 3,280,824 10/1966 Roberts 13l17 1 OTHER REFERENCES Chemical Abstracts, pub. by the American Chemical Society, vol. 53, No. 19, Oct. 10, 1959, 17998(i).

SAMUEL KOREN, Primary Examiner.

MELVIN D. REIN, Examiner. 

1. A DOMESTIC TOBACCO HAVING ADDED THERETO A SMALL AMOUNT OF 1-METHYL-2-PYRROLECARBOXALDEHYDE SUFFICIENT TO ALTER THE FLAVOR OF THE TOBACCO. 